Enantioselective Synthesis of (−)‐10‐Hydroxyacutuminine
Denise C. Grünenfelder, Raul Navarro, Haoxuan Wang, Nicholas J. Fastuca, John R. Butler, Sarah E. Reisman
Abstract
An enantioselective synthesis of (-)-10-hydroxyacutuminine is reported. Central to our strategy is a photochemical [2+2] cycloaddition that forges two of the quaternary stereocenters present in the acutumine alkaloids. A subsequent retro-aldol/Dieckmann sequence furnishes the spirocyclic cyclopentenone. Efforts to chlorinate the acutumine scaffold at C10 under heterolytic or radical deoxychlorination conditions led to the synthesis of an unexpected cyclopropane-containing pentacycle.
Topics & Concepts
Enantioselective synthesisStereocenterCyclopentenoneCyclopropaneCycloadditionStereochemistryChemistryOrganic chemistryCatalysisRing (chemistry)Alkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsBerberine and alkaloids research